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【结 构 式】 
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【分子编号】62491 【品名】ethyl 3-chloro-3-(3-pyridinyl)propyl(methyl)carbamate 【CA登记号】 |
【 分 子 式 】C12H17ClN2O2 【 分 子 量 】256.73196 【元素组成】C 56.14% H 6.67% Cl 13.81% N 10.91% O 12.46% |
合成路线1
该中间体在本合成路线中的序号：(VI)Similarly, thiazepinone (I) was transesterified with isopropenyl acetate (V) to afford acetate ester (IV). Subsequent alkylation of the lactam N of (IV) with 2-(dimethylamino)ethyl mesylate (VI) in the presence of K2CO3 furnished diltiazem. Similarly, thiazepinone (I) was transesterified with isopropenyl acetate (V) to afford acetate ester (IV). Subsequent alkylation of the lactam N of (IV) with 2-(dimethylamino)ethyl mesylate (VI) in the presence of K2CO3 furnished diltiazem.
| 【1】 Harsanyi, K.; Gizur, T.; Demeter, A.; Aracs, Z.; Felmeri, J.; Berki, K.; Trischeler, F.; Vincze, Z. (Gedeon Richter Ltd.); Process for the preparation of benzothiazepin-4(5H)-one derivs.. ES 2001146; JP 1987108872 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 62436 | (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one | C16H15NO3S | 详情 | 详情 | |
| (III) | 62488 | (2S,3S)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one | C20H24N2O3S | 详情 | 详情 | |
| (IV) | 62490 | (2S,3S)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate | C18H17NO4S | 详情 | 详情 | |
| (V) | 21178 | isopropenyl acetate | 108-22-5 | C5H8O2 | 详情 | 详情 |
| (VI) | 62491 | ethyl 3-chloro-3-(3-pyridinyl)propyl(methyl)carbamate | C12H17ClN2O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)Treatment of nicotine (I) with ethyl chloroformate produces the open-chain chloro carbamate (II) which, upon distillation, undergoes elimination to the N-pyridylbutenyl carbamate (III). Acidic hydrolysis of the carbamate group of (III) then provides the target metanicotine
| 【1】 Acheson, R.M.; et al.; Transformations involving the pyrrolidine ring of nicotine. J Chem Soc - Perkins Trans I 1980, 2, 579. |